Benzenesulfonyl chloride → HCID 86760979, compound

HRID 1432952Notes

Reaction equation

HRID 1432952 reaction equation
[OH-].[Na+].[C:3]1([S:9](Cl)(=[O:11])=[O:10])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:13]([O:20][C:21]([N:23]1[CH2:28][CH2:27][N:26]([CH2:29][C:30]2[NH:38][C:37]3[CH:36]=[CH:35][N:34]=[C:33]([Cl:39])[C:32]=3[CH:31]=2)[C:25](=[O:40])[CH2:24]1)=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>[N+](CCCC)(CCCC)(CCCC)CCCC.[O-]S(O)(=O)=O.C(Cl)Cl>[CH2:13]([O:20][C:21]([N:23]1[CH2:28][CH2:27][N:26]([CH2:29][C:30]2[N:38]([S:9]([C:3]3[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=3)(=[O:11])=[O:10])[C:37]3[CH:36]=[CH:35][N:34]=[C:33]([Cl:39])[C:32]=3[CH:31]=2)[C:25](=[O:40])[CH2:24]1)=[O:22])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 53757606Phenylmethyl 4-[(4-chloro-1H-pyrrolo[3,2-c]pyridin-2-yl)methyl]-3-oxo-1-piperazinecarboxylate

Product 1

HCID 86760979HCID 86760979, compoundYield 98.1%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Powdered NaOH (0.96 g, 23.9 mmol) followed by nBu4NHSO4 (0.32 g, 0.96 mmol) and benzene sulfonyl chloride (1.8 mL, 14.1 mmol) is added to a solution of 4-(4-chloro-1H-pyrrolo[3,2-c]pyridin-2-ylmethyl)-3-oxo-piperazine-1-carboxylic acid benzyl ester (3.81 g, 9.56 mmol) in CH2Cl2(32 mL) at RT. The resulting slurry is stirred for 3.5 h then diluted with CH2Cl2 and washed with saturated NaHCO3 and brine. The organic layer is dried over MgSO4, filtered and concentrated to dryness. The crude product is chromatographed eluting with 1-5% MeOH/CH2Cl2 to yield the title product (5.06 g, 9.38 mmol). 1H NMR (CDCl3, 300 MHz) δ8.23 (d, 1H), 7.97 (d, 1H), 7.84 (d, 2H), 7.61 (d, 1H), 7.51 (m, 2H), 7.38 (s, 5H), 6.50 (s, 1H), 5.18 (s, 2H), 5.03 (s, 2H), 4.29 (s, 2H), 4.29 (s, 2H), 3.80 (m, 2H), 3.51 (m, 2H). Ion spray [M+H]+=539, 541, Cl pattern.

Workup

  1. washwashed with saturated NaHCO3 and brine
  2. dry with materialThe organic layer is dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated to dryness
  5. customThe crude product is chromatographed
  6. washeluting with 1-5% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-5ebdf93f370b4244ac2be3ab1a28ed16
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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